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Season 1 · Episode 1 September 15, 2026 45 min

Building a Social Security Disability Practice After a Catastrophic Injury with Diane Haar, Hawaii Disability Legal Services

Diane Haar

Founder, Hawaii Disability Legal Services — Honolulu, Hawaii

Episode notes

Diane Haar was a war crimes litigator when a catastrophic accident nearly ended her life. She was denied the medical evacuation she had paid for. She came out of recovery knowing disability law was where she had to be.

She founded Hawaii Disability Legal Services in 2012 and represents claimants across Hawaii, the Pacific Territories, and the Philippines, most of whom find her by word of mouth. She still sits in homeless shelters doing applications herself, and she bootstrapped a paperless firm by coding her own case management system before she could afford to buy one. When we called her a systems thinker, she corrected us.

Diane Haar is founder of Hawaii Disability Legal Services in Honolulu, Hawaii.

In this conversation:
  • The Person: her sister, the accident, the denied evacuation, and why she still does applications in homeless shelters herself
  • The Bootstrap + Book of Business: starting with no loans and banker boxes, coding her own case management system, and how word of mouth reached the Philippines
  • Survivor, Systems & AI: the solo years, what she automates now, and where AI breaks down on a brief
  • Build It or Buy It: when to build your own tools and when to stop
  • Takeaways: what she tells people starting out
"What I actually am is a survivor."

"They don't need the shiny fancy office. They need you to win their case."

This conversation was lightly edited for clarity and never for message.

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Transcript

Lightly edited for clarity and never for message.

Diane Haar (00:00) This was said to me after a hearing, and it's so true, and it's so true so often. And what he said was, I wrote it down. When I was well, I helped so many people, I never turned them away. Then when I got sick, there was no one there who would help me. And I remember him saying that. He was crying to me when he said it. Will Yang (00:41) My guest today is Diane Haar, who founded Hawaii Disability Legal Services in 2012 and represents claimants across Hawaii, the Pacific Territories, and the Philippines, most of whom found her through word of mouth. In this conversation, we get into how a war crimes litigator survived a catastrophic accident, was denied the medical evacuation that she had paid for, and came out of recovery knowing disability law was where she had to be. We talk about why she still sits in homeless shelters doing applications herself. And how she bootstrapped a paperless firm by coding her own case management system before she could afford anything else. When I called her a systems thinker, she corrected me. She's a survivor. And the backdrop behind Diane, this whole episode, is Saipan. Stay to the very end to hear why she chose it. Will Yang (01:23) Well, Diane, I'm so excited to have you on Disability Heroes. You your story in disability starts with a deeply personal one. I'm curious, how did you land in disability law? Take us back to that moment. Diane Haar (01:34) I feel like everything kept pointing me to this area of law. I was born into a family with a disabled older sister, and I was the youngest, and I would watch how people treated her. And most people were fine, some weren't, but they do things in front of me that they didn't think I understood since I was a little kid. And from the time I can remember, I always wanted justice for her. I wanted justice for people who couldn't speak for themselves, who couldn't advocate for themselves. And You know, when I went to law school, it was primarily for that reason. I wanted to advocate for people who couldn't advocate for themselves. But I felt like representing folks with disabilities hit too close to home. And I just I had this picture in my mind, you know, of just being in a courtroom and bursting into tears. And I didn't want that to be me. So I went into other things at first. So I was actually a war crimes litigator. And I was in this massive accident. And it had a long recovery. And, you know, I had the fight. I had student loans. I didn't have medical insurance. I didn't have any money to live on. I didn't know I was gonna pay these loans. You know, suddenly I'm in the fight too. It was the final nudge that when I recovered, when I could go back to working. I understood at every fiber in my being, at every level, why the disability benefit systems are there and why they're so needed. And this is where I had to be. So this is actually what launched my practice. Will Yang (02:58) When you were in that moment and the system failed you, what do you remember thinking about in terms of then this source of inspiration for you to want to fight for others, and in the system that is so important for so many? Diane Haar (03:12) It wasn't a perfect thought process. As these things go, when you have major traumatic life events like this, you know, the story we tell, it was all seamless, it was all beautiful, that's not it at all. I was railing against what happened for what was probably the 80th time. You know, I was upset about the accident, I was upset because my future had changed. This wasn't what I planned, this wasn't what I'd worked for. And someone said to me, and I still remember this, he said to me, You've gotta stop. You've gotta find the meaning in this. If you don't find the meaning in this, it will eat you alive. And he was absolutely right. And the meaning was exactly what I just told you, which is, it was teaching others what I had to learn to survive. It was teaching others and giving others what I needed to survive back then. The benefits to live on, the medical insurance. And it was also the peripheral stuff. It was, you know, for my folks that I represent who aren't gonna get better, teaching them how to get loan repayment when they're not gonna be able to go back to work when they are permanently disabled. Will Yang (04:11) I'm curious when you think back to your life experiences and then how you show up as a disability advocate what are the underlying principles that you stand by as a result of your own lived experiences at this point? And how do you express those in terms of the ways that you meet your clients at where they're at today? Diane Haar (04:33) Because been doing this for quite a while now and when I first started You know, I was just two seconds away from being where they were at. When I first started my law firm, I went to the homeless shelters. I mean I was actually invited in. I was the only attorney that did this. I think I still am the only attorney that does on a regular basis. You know, I'll sit with my homeless clients and sit in the shelters and do their applications and do their appeals and talk to them. But when I first started, I was only two steps away from being where they were at. One of the things I've noticed is the longer my firm has existed, the longer I've been okay, the longer I've, had money coming in and a safe place to live, the further we can get mentally from being in that space. So I feel like I need to remind myself of where I came from. I just see this in myself. I think this is what happens to those of us who start from this place of knowing what it was like to be there. I think we have to continue to remind ourselves of what it was like to be there. And you know I have writings that I did early on that I can go back and read that really remind me of what what it was like when it was really raw. And there are other things as well. Because we can get too far removed. And I don't ever wanna lose the empathy. I don't ever wanna lose the understanding of what it's like to be the person who's so dependent on the help of others and others that I don't even know. I don't wanna lose what it's like to be the person struggling. And I don't wanna lose the understanding of one of the unfortunate things that happens when folks become disabled, and this is a lot of folks, you find out who your friends really are. You find out who is gonna be there to support you. And it tends to be a smaller group than we realized. And that can be really tough too. I don't want to lose the memory of that because I don't want to lose my understanding and compassion for the people going through it. Because they're struggling with a lot of things, not just the disability but those realizations. And sometimes folks can end up attacking us, the person who's trying to help them, just out of the confusion of that. I don't want to lose what I understand because I don't want to lose my compassion. Will Yang (06:40) How do you manage to regulate your own emotions in those moments when you're sitting with your client in the homeless shelter and recognizing also when they just want your presence versus advice or some other line? Because I there's an art to that, right? There's an art to understanding when sometimes there don't need to be any words said and in other times, How do you balance those different pieces and then also what's going on in your own mind and your own feelings in those moments with your clients? Diane Haar (07:08) get it right. You'd have to ask the people I represent because I suspect I don't always get it right. Sometimes I'm probably talking when I should be listening and vice versa. But I'll say as far as regulating my own emotions, having been through it myself, stuff comes up. And I feel like when things are harder for me emotionally, I'm probably exactly where I need to be, and I need to be present and I need to be, taking a look at that and working through that as well. So sometimes, at the same time I'm helping them, I'm helping myself. Will Yang (07:38) That makes sense. You've mentioned before that, you know, you have this firm ethos of not wanting to leave anybody behind. What does that mean to you in terms of how you then run your practice the right way through all the years representing all different folks from all different sides of, more, more lesser known pockets of the U S I would say. Diane Haar (07:56) So I'll say part of my story. When I had my massive accident, when I was a war crimes litigator, I had medical evacuation insurance, and I was denied medical evacuation. And that's a big thing for me. It would have made a difference to my recovery. It would have made a difference in a lot of different ways. So that's a big part of my not leaving anyone behind. The help I finally got was from U.S. Service members, and that was the first time I heard that, because they made it really clear to me, you know, "We don't leave people behind." For me, I didn't choose to actually come out to Hawaii. It was with my husband's job. And I knew when I came out here that I'd have to open my own firm because there was no one else doing what I did. But because there was no one else doing what I did, it also meant that there was a lot of people who needed help or they were gonna get left behind. And that was particularly in the US territories. So the Pacific Territories, Guam, the Marianas Islands, and American Samoa, there were no attorneys doing what I did. There was no one helping put together the medical records. There was no one putting together the argument. There was no one showing up on their soil to talk to them and represent them. So a big part of leaving no one behind is going to these places and meeting with these people. Another part is what I said before of going to the homeless shelters and talking to them and listening to them. It's finding the people who don't necessarily have the normal referral sources, who don't know to call the bar association to find me. It's knowing where they live and showing up where they're at. Will Yang (09:24) In terms of showing up where they're at, there, what are some of those things that you've learned just sitting in the room folks as opposed to what you might have previously, only caught over video? Diane Haar (09:34) so many different things it's hard to know where to start and part of part of what I want to talk about some of the most fascinating things I've learned these US citizens that that live in the territories their stories. I've learned what it's like to grow up in the territories. What it's like when you are a US citizen and you know it and nobody else does, you know, when you call someplace on the mainland and they act like you're from a foreign country. I've learned so much about so many different cultures. Even Hawaii. You know, Hawaii isn't like the mainland US. There's so many different cultures here and the culture itself is different from the mainland US. And just sitting back and listening, I've learned so much about people's fears and frustrations and hopes and dreams that are different than what I learned growing up in Southern California. Will Yang (10:21) What are still true? Like, I'm curious when you share that of all these different experiences and perspectives that you've had, what do see that is still true across the shared human experience on that side? Diane Haar (10:31) We need each other. Everybody needs an advocate. Everybody needs folks that care about them. Some folks don't have an intact family structure that they can depend on. And they need the relationships either, you know, with other people, with case managers, with me. Everybody needs support. One of the things that's actually genuinely true across all cultures, everybody has value. And this is something that's really frustrating too, is we hear it a lot, you know, people putting down other cultures, people putting down other people, people putting down people for being homeless. Everybody has value and that is something that is universally true. Sat down with a lot of people that are just forgotten about it it seems like, whether it's far from the mainland US or it's in the homeless shelter. And I feel like everyone has has told me things that make them genuinely human. They don't deserve to be left to die. Will Yang (11:25) And in those moments when you're able to stay with them, and I'm sure they recognize that this might be one of the few times that someone is seeing them for their story and their experiences as well. When it came to starting your firm, I'm curious if you can take us back to the moment when you recognize that there is this dire need for representation and advocacy in these areas and also what you wanted your firm to be about. Because my understanding is it's around 2012. And you set out saying, this is going to be a paperless firm. You know, there's going to be certain things that you do things your way. And, I think this section would be useful for other practitioners that might also be thinking about how they build different processes. So take us back to that moment. What are the things going through your mind as you're going through like that initial business formation stage? Diane Haar (12:12) So I was terrified when I first started my law firm and it really was a case of I had to start it or I could not do this area of law because there was no one here I could go to work for. I also didn't want to take any loans to start my practice. I don't know that I could have, but I didn't want to. I still had student loans, which was terrifying Will Yang (12:28) Hmm. Diane Haar (12:29) enough. So I was trying to figure out how to do it all on my own. I wanted to be paperless. In part because I live in an island state and the only way to get from island to island and truly have your whole office with you is is to have it on your laptop. But the other big thing is when I was a war crimes litigator, we were paperless there as well. I just didn't want the paper. I didn't want all the excess stuff. Before I'd put myself through school, while I was still putting myself through school, I worked for these law firms and it was back before paperless anything. And they would pay lots of money to rent these spaces to store these banker boxes full of files. And they were dusty and smelly and my first jobs when I had no skills was going through those boxes. I remember I had one I worked for one law firm where I was taking paper clips off these old papers because they were saving paper clips. It was awful. I mean they were dusty by the end of the day it was dirty. It it was not a great experience. There wasn't a whole lot of air conditioning. It was not good. I wanted paperless. I did not want that. In addition sorry now I'm going off on the paperless bet, but there's certain things you can do with paperless stuff. You can search the files a lot easier, you know, you can do your word searches, now you can use it for generative AI. So it's really the backbone of the firm. But that was the start. So I started, I wanted to be paperless, but I also didn't want to spend money. So I was extremely fortunate in that I was familiar with coding. Not a hundred percent familiar. I'm foremost a lawyer and some of the stuff I had to Google and figure out. Back in 2012, I coded my own first case management software. And I used some of the tools that I'd used when I'd worked for law firms before law school. You know, and those tools, I mean, I learned how back then how to really use Word. And I really advocate this as well. Learn how to merge documents, learn how to really use it. There's a lot of things in there. That case management software will do for you, that Word will also do if you can't afford the case management software yet. And I don't advocate going without case management software forever. But learn how to really use your word because you're already paying for that. You don't need to double pay for things. So I had that. Another thing when I was starting, I couldn't afford marketing. So one of the things that was happening is there was a lot of marketing from firms that weren't here in Hawaii. And I had to compete with that as well. One of the most valuable things that I did and I learned it on the back end because I was doing it on the front end because it's what I wanted to do. But I became part of my community. I became really involved with the Bar Association, giving CLEs, I became really involved with the homeless shelters, you know, going out and working with people. I became really involved with local organizations. If you become part of your community, that itself will market your practice. People will learn your name. And in fact that actually built my practice for a really long time, probably still does. My practice is still primarily word of mouth. One of the things that I made sure of. If I said I was gonna be there, I went. I didn't stand people up, I wasn't late, I showed up. Don't be the person that doesn't show up. Don't be the person that says you're gonna do something and doesn't do it. That'll ruin your reputation in seconds. Honestly, my book of business was built. Primarily by going to the homeless shelters and that's you know, you call and you see if you can come in and you talk to about what you do. And that's exactly what worked. And it didn't take very long because I found that not too many people wanted to do that. Pretty soon the case managers are calling me and they still do. That was actually how my book of business got built up was word of mouth. I was the person that would show up. And I did do workshops as well, primarily for the case managers, And it's to tell them, who is eligible for these benefits, who isn't eligible for these benefits, things that help people get these benefits, you know, going to the doctor. The little things that we know that that other folks may not know, and that way they can help their folks as well. You know, making sure they go to the doctor, Making sure they're hooked up with Medicaid, those little things that also help us win their case. Will Yang (16:32) What's going to be true is the part of presence here. It's like you are showing up and being present with these people. You're doing on a consistent basis so they know to expect you to be there. And sometimes it's the simplest things in business that, you know, actually drive the most value as well. You had mentioned earlier as well that there were some unlikely or just sources of referrals that you wouldn't have thought of. Do you have any of those that come to mind just when you think about, you know, where you've heard of potential cases coming from? Diane Haar (17:01) It's really blown me away. I think the craziest was when I started getting cases out of the Philippines. And I was asking them, how'd how'd you know I did this? And it was word of mouth. And that just absolutely blew me away. But I'd represented people in Hawaii who went back to the Philippines to make their home after they gotten benefits and they were telling their friends, so they were calling me. My name has also gone word of mouth through the territories once I started going out there, but through all the Hawaiian Islands. And it still blows me away. I grew up in Southern California. I didn't grow up here. And this is a place where it really matters. Growing up here, being from here really matters. I'm super honored that people trust me and that they're willing to to work with me. That said, I now have people working with me in my law firm who are from here. And that helps as well because they do have that that background too. Will Yang (17:49) Yeah. And I think one of the takeaways that I'm hearing is it was from your commitment to the community that they then accepted you as one of their own as well, even though you didn't come from there. I think showing up again over time gets you there as well. Will Yang (18:02) Let's take a second for our sponsor. This episode is brought to you by Chronicle. More than 2,800 disability professionals use Chronicle to stay on top of SSA activity. Chronicle gives you daily ERE checks, e-file updates, deadline visibility, and all without the manual work. It's built specifically for Social Security Disability practices so that there's no configuration overhead. Chronicle monitors the portal, tells you what changed, and gives your team back hours of time from logging in and checking automatically. You can learn more at chroniclelegal.com. Now back to Diane. Will Yang (18:32) You're in this bootstrap stage and you don't want to spend any additional money. You know, you've got these other loans and obligations to account for. How do you, in those moments, recognize, what is truly essential versus non-essential in terms of drumming up your first business? There's always somebody out there that's trying to sell you something saying like, this is going to help you get business. But that's not actually true, right. And we can, we all know that. And so I'm curious in those moments, if you try to think back at that bootstrap period, you know, how did you prioritize, for example, knowing that whether it was you coding up your own case management system, that you would need something like that from a process standpoint for your firm or just in general, like, what did your team evolution look like at that time? Obviously you were probably doing a lot of this yourself at that point. So like, how are you thinking about that in relationship with the paperless idea or like the ethos behind being paperless in the future as like the foundation or the backbone of the firm? Diane Haar (19:27) I'll say I was a solo and by a solo I mean all by myself, no support stuff for the first couple years. And I'll say things have changed now with starting up because you have a few extra pieces of help with generative AI that I didn't have back then. But one of the ways that I really knew how to prioritize. Wouldn't it be great if law school taught us, and I'm actually a huge advocate of this and have been for years. Not that the law schools have ever listened, but starting your own business, like learning how to do the business skills. I knew what I needed in a law firm because I had to put myself through. I was broke. I actually paid for all my schooling on my own. I either got scholarships. Or I paid for it. I took out the loans, I paid them back. Every single penny was me. Which also meant that I worked and I worked in law firms. I knew I needed case management software because that's what they used. I knew how to write a letter because people who were administrative assistants who sat me down and taught me how to do it because that's exactly what I had to learn to do for the attorneys I worked for. I knew how to do it because before I went to law school, I had been law firm administrative staff in every capacity. But wouldn't it be great if law schools also taught that? I think it's a s it might be essential when you're starting out as an attorney. But wouldn't it be great if they also taught us how we could also have the freedom of becoming a solo? Or if there's no one we can work for, how we can work for ourselves. And I think that's becoming more vital because with generative AI, It is now taking over a lot of the new attorney jobs. It's taking over a lot of the associate jobs. So a lot of the places that new lawyers would have gone to learn the practice are no longer available because of generative AI. I feel like it's crucial that these young graduating attorneys, that their only contribution to the system should not be tuition dollars so that the law schools can stay in business. I think the law schools need to give back as well and give them the tools that they need to start their own practices because they may not have a choice. And they shouldn't have to pay back their student loans by working at Starbucks. They should be allowed to do it as an attorney. And that also goes with and now I'm getting on my soapbox, you know, generative AI has really taken off over the last couple years too. And I will say before generative AI, I did a lot of automation. I don't think that all attorneys need to be able to code the way I code. But I think they should know what automation is. I think they should be taught what exists. I think they should be taught what's useful and what's not. And with generative AI, I think that should be a component of law school now. I think the law schools, including the one I went to that's been very vocal about what it's not gonna do, are doing this their students a huge disservice. This is the future of the practice. And it is something that new lawyers need to know if they're going to find their place in the practice. Will Yang (22:11) I think something that's really cool about the generative AI side of things is it democratizes so much of the access to different information. Because if you think about it, it's essentially a supercomputer of every other respective domain. And what it allows is for people with high agency to essentially just like unblock themselves if they're just curious enough to do so. Right. And it sounds like what I'm hearing from your experience in these early bootstrap days was A lot of it was sparked by either the tapestry of experiences that you had had up to this point at these different firms, or it was your own intuition or curiosity that was driving you to then the next solution point. And what you're doing in that process is you're practicing your real-time problem solving to then run a business. And then from there, you're starting to scale up the processes and systems. That's something that always has struck me in our conversations is that you're very operations and systems oriented thinker. I'm curious if you... Where to be pushed on this side of it, where do think that comes from? Like over the years, as you've run your practice now for over a decade, how have you honed that attribute in terms of that strength of yours? Because as you mentioned, even in the pre generative AI side, you were already thinking about automations or improvements and whatnot. So where does that all come from? And like, how have you honed that through the years? Diane Haar (23:31) It's funny when you said a systems thinker, when you originally said that to me in a different conversation, I had to go and look it up 'cause I didn't know what that meant. You know what I actually am is a survivor. So I just confess that I put Will Yang (23:43) Hmm. Diane Haar (23:43) myself through school. I did things on my own because the resources weren't there. And that's exactly how I approached running the practice. It's exactly how I approach most things in my life. And it's in a lot of ways in generative AI what's gonna separate those who can from those who can't. You know, you have to have the will to make it happen. You have to throw yourself all in. It's sink or swim. It's kinda when you're a little kid I I doubt they do this anymore. When you're a little kid and they throw you in the deep end of the pool and it's like either you go to the bottom or you figure it out. That's how I've actually done all these things. That's when you're saying a systems thinker, it's this is my livelihood. This is my survival. The reason why it's all why I figured it all out is 'cause I had to. Will Yang (24:31) Hmm. Diane Haar (24:31) Because there was nowhere else to go. I will say AI and generative AI is gonna make that a whole lot easier for the folks coming up. 'cause they're gonna be able to ask questions to the LLMs that I didn't have access to, but I at least had Google. I guess if you could write a prompt, if you don't consider yourself a survivor or you haven't had to be a survivor, if you can write a prompt and have that prompt help you think that way, or question you and you know, give you answers as to what a survivor, someone that is looking at this as their sheer survival would do or say, that actually might be a good start. Will Yang (25:06) can say from personal experiences that adding something to the version of, this is a set you absolutely must do this or you will lose your job or something can lead to some interesting outcomes in terms of what a generative AI model will give you. On that on the side of you starting to formalize and get out of that bootstrap stage to now having members of your team, like for folks that are listening that want to think about how to scale up and getting past that bootstrap stage into that next next stage of growth. You know, how did you approach that? You've been very efficient in terms of how you've done that. And I'm curious, like, when do you think about, you know, making a particular set of the work into somebody's job versus something that is going to go through an automation through a system? Like what are the things that still require human touch, versus, something that requires just you to automate a system or workflow. Diane Haar (25:59) So the automation That's also been a survivalist thing. So I live in an island state, and there are only so many people. And It is hard to find employees here. The employment market is really good for employees because there is so much need and so few people. So I automate and it's always been this way, I automate the things I can't find. I prefer to have people around me. I was never looking to save money. But I automate for the things that I can't find. The other part of that is my firm was created and still exists on a human connection. And I've also found that the more I automate for the folks that I could find, the folks that do work for me, I'm trying to give them more time to talk to clients, to talk to potential clients. I'm trying to give them more time to make those connections with people. So that's where I automate as well. Will Yang (26:49) Yeah, that makes sense. And you have said before that, you know, AI is pretty much kind of like you having an associate now. And you still have to read cases, but you know, have there been cases where you see limitations in terms of what AI can do for you and what it still cannot do for you, maybe on the point of like the human connection points, obviously, but what are other things where you see hallucination risk and, you know, just other issues as you've been tinkering on the AI side of things? Diane Haar (27:16) I still see the hallucinations. There's still a lot that AI can't do. You know, I do federal court briefs as well for both practices, Social Security and the VA disability. I would never write a federal court brief from scratch with AI. I still do I still use briefs from scratch. I'll use prior briefs that I've written. I'm looking up the cases. I use AI for federal court briefing mostly for proofreading. Something that I found that I really like using AI for is writing for specific judges. You know, some judges are really new and I want to explain more, and when I'm proofreading, I'll write prompts devoted to like a judge that's new explaining more. For a judge that's been around for a while, if there's certain things that I know they like, like if they like brevity, I'll I'll prompt it for that. But the other part of that is I'm also checking it after it does the proofreading because I've noticed it can also sometimes change the meaning of my sentences. So I'm still having to double check stuff. I don't know that that's ever gonna change. I mean that is being an attorney, right? I'm a supervising attorney even when my associate is generative AI. But the other part of that is I also don't feel it can write freeze from scratch. And I'm still hearing lawyers talking about getting in trouble for, you know, the paralegal or the contract attorney that they use that wrote handed over a brief that was written entirely by Generative AI and it's hallucinated. So it's also watching out for that as well. Will Yang (28:48) One of the things I wanted to make sure we cover too was, right, So you were in the bootstrap days, you made your own case management system. There obviously was a time and place for that because you couldn't afford anything else at that point. But at what point did you decide to let that go and go commercial because, Eventually the thing probably had its quirks or bugs and, know, it's time to kind of level up. How did you assess those moments? Take us back to the moment to really start investing in other providers to solve some of these problems for your firm. Diane Haar (29:18) I will say I'm always really clear about this. I can build things, but I don't want to have to. I built my own first case management software because I couldn't afford commercial stuff. I went to the commercial side as soon as I could afford it. I already knew which one I was gonna get, that's the one I went with, that's where I went. It's the same with things that I do now. I am always happy to tell folks like you guys, like Chronicle, exactly what I'm doing, because if you'll build it, I don't have to fix it. To fix it and the other problem is I built my own case management software but if you look at case management software the technology keeps changing and I'm a lawyer foremost I'm a lawyer and I strongly believe if I spread myself thin too thin and I actually know if I spread myself too thin I'll be a terrible lawyer So I don't want to be doing all the technology plus the lawyering. Because, you know, then at best I'll be a mediocre lawyer with mediocre technology. I only do the technology side on my own if it's not already there. But I'm always happy to tell folks who do technology a hundred percent of the time exactly what I'm doing, because if they'll build it and fix it and maintain it, I can go back to lawyering full time, which is what I chose to do. Will Yang (30:39) Being somebody that is so tech friendly and an early tech adopter, what have you noticed as some patterns across all the different vendors you've used in terms of what makes for a quality product from a legal technology standpoint? I'm sure you've also seen your fair share of the flybys that don't really sustain themselves. If you're answering this for a listener who's starting to evaluate different legal solutions, what typical advice do you tell? You know, a firm owner or a case manager that's starting to explore different solution concepts to look out for when they're in that tech evaluation process. Diane Haar (31:15) Talk to other people in the same practice area about what they're using. I have seen a lot of flyby nights, and I also see a lot of people really overselling what they've done. And you know, I I understand there's a huge gig economy and there's a lot of people trying to make their name and trying to make a few dollars. There's a lot of really bad stuff out there. There's a lot of people that will just take your money and They're not gonna update it either. It's terrible stuff. So it really is talking to other people about what they use and looking into the product itself. I mean, they should offer a demo. The demo will allow you to talk to their people, don't just talk to the salespeople, because sometimes sometimes they have amazing salespeople. And their tech support, what tech support? It's one of the things Well you guys, I mean it's nuts. Chronicle is nuts. You're really responsive. This isn't supposed to be a plug for you, I know, but that's one of the things that's really amazing. The companies that are responsive, the companies that answer back. I will say the commercial case management software I went with, they have gotten really big, but when I decided who I was gonna go with, it was one guy shilling his product. I'd sat through a CLE, I had fashioned my own case management software on their one of their earliest versions, you know, and It's been a really responsive company too. So yeah, do your homework. Make sure you get the responsiveness, make sure there's other people using it, and don't go with something some friend's nephew has built. Will Yang (32:50) I think you hit on two really great points that we also often recommend, folks, which is the responsiveness point for sure. Because when things break, that's what you should expect in terms of the back end of that. And then the second point was the specificity to the type of law that the solution does. So something that we see a lot is folks that oversell themselves because, you know, they're trying to cater to all these different legal markets, but they don't actually uniquely understand the specific workflows that a disability firm needs to do versus, you know, even something that's closely similar, like personal injury and whatnot. But it's something which like there's sometimes overlaps in firms that do both. But the work itself is still different. So understanding somebody that's actually going to have that specificity of the context and those small quality of life things that will then be incorporated into the software, like something as small as a date last insured being available or AODs being available and whatnot. So that's just a small, small thing that I would say from what you had just mentioned there. Diane Haar (33:48) That actually really is huge because I'm in a niche practice, as you know. And I have seen those things. I mean, even my case management software when I first started using it, I was actually the one that dragged them to their first NOSSCR conference, and I'd been begging before that because I needed them to understand my practice area so that they could better cater to it. So as Will Yang (34:06) That makes sense. Diane Haar (34:08) as grateful as they were for the extra business on the back end, It was actually for selfish reasons, so yeah. If they're listening, Will Yang (34:15) Yeah, that makes sense. Diane Haar (34:16) I love you guys, but yeah, that that was really why. Will Yang (34:18) As we start to wrap up, you know, a couple of soundbites that I'd love to capture. The first one is, what is one thing about representing clients in the Pacific that you wish the disability law community on the mainland would understand? Diane Haar (34:32) Representing clients in the Pacific are not the same as clients on the mainland. There really is a different culture out here and also a different set of circumstances. We're really restricted in what medical care we can get. So Hawaii we have more medical care, but it also varies by island. You know, where I am in Honolulu I actually have view of our county hospital and I just this morning saw the Life Flight helicopter landing on it, bringing someone in probably from one of the neighbor islands, someone that something terrible had happened to. On our neighbor islands there's not as much medical care. In the territories there's definitely not as much medical care. They often come to Hawaii when they need more specialty care, and we all have to go to the mainland when we need more specialty care. And that's a really long thing to say, but it's important. Because sometimes we have to form as attorneys bigger arguments. Sometimes we really have to stretch to get people approved. Because, American Samoa or Saipan, one medical facility, you're dealing with one medical facility and specialty care is when specialists fly in. But these people are going to die if they don't get benefits. They're not going to be able to stay in their homes if they don't get benefits. To do the extra work to get these people approved. It's not just throw everything in the wall and see what sticks. Will Yang (35:52) When you think back of overall when you're starting your firm, were there ever any points where you thought about doing something else when we talk about the entrepreneurial calling, there's often this moment where you feel like everything comes to a head and you're like, I'm going to either do this or I'm not. And I'm curious, Where did the boldness or the, the kind of little nudge inside your head come from in that moment to give yourself the confidence that yes, like we have to do this because, you know, to your point on the survivor thread, it's this or, or nothing else at that point. And how would you encourage or motivate somebody that you think might be at another firm? Maybe they're working in a larger firm. They're thinking about starting their own business, but they've got all these other silent. You folks on their sh—things, characters on their shoulder that are essentially telling them like, you could maybe do this, but maybe not. Diane Haar (36:47) Which moment of doubt do you want to talk about? So I'll say when I started my own firm, when the choice was there, I think it would have been a lot harder if there had been some place where I could have gone and applied for a job. I didn't have that option. So the choice was really: if I wanted to continue doing disability law, I had to start my own firm, period. Even after I started it, when I say which moment of doubt did you want to talk about, there were times where if someone had offered me a job and offered to pay me a certain amount of money, I might have jumped ship because, it's a contingency fee practice, so you don't make money for a while. And there's different points where it's just scary. I mean You know, there's there's the moments of doubt, there's the am I gonna make it? There's the how am I gonna pay the bills? It's contingency fee and you're sitting there wondering if you've won your cases. I mean, you know, there there's a lot of moments of doubt. What I'd say is Before you start the practice, decide how long you're going to do it for. Are you gonna do it for one year, five years. Before you, if it's not successful, you'll give up. Set a number of years. And that way, when you're doing it, you're not gonna quit before that number of years is up. Because there were moments where I really questioned it in the beginning, where I really thought, "This isn't gonna work," You know. And it did. And the only thing that saved me was nobody came out and offered me a great paying job right at that exact moment. Because I would have jumped ship. So, for the people with where that might happen or who are sitting in a job, just set a a number of years. And also, think about when your retirement age. Are you gonna look back and always regret that you never did this? Will Yang (38:29) think that regret minimization framework is so valuable there because worst case scenario, you were able to help people that were in serious need at their most vulnerable moments. Best case scenario, you do that and you build a successful business. And what would you tell a disability attorney who's thinking about starting their own solo practice before they make their first mistake? Diane Haar (38:50) Shoot. Narrow down all the different mistakes I've made and see what I would actually say is Don't spend money you don't need to spend. Keep it as minimal as possible. At the end of the day, the biggest thing that your clients need and want from you is for you to win their case. They don't need the shiny fancy office. They don't need the latest and greatest equipment. They need you to win their case. So when you're first starting out, focus on what you need to win cases. And focus less on your appearance and your firm's appearance. Will Yang (39:28) Moving into our lightning round, the first question I have for you is what is the SSA form that you hate the most? Diane Haar (39:36) Can we please automate the SSI applications? I don't understand. We've been able to do Social Security disability applications online forever. SSI, especially right now, this has been nationwide, people are noticing that Social Security, depending on where you're at, wants different things. Out here, We have to do the long form paper SSI application and send a wet signature. They won't accept faxes, they won't accept anything else, and we have to send it certified because it gets lost. So we need to prove to them sometimes that they actually received it. It's been a lot of years since the Social Security Disability Insurance application was made so it could be done online. I don't understand why we can't do this for SSI, for our most vulnerable citizens, for the people that most need the help. I mean, these are our low resource, might not even have a home, folks. I don't understand why we can't do this online, why it's not automated. So that's that's the one I want. That's that's exactly what I want. Will Yang (40:40) What is your biggest pet peeve when it comes to ALJ behaviors? Diane Haar (40:45) mess up to my clients. I know ALJs can have a bad day. I don't like it when they take it out on me, but I would very much prefer they take it out on me. My clients, you know, this is a big deal to them. I know ALJs see a lot of folks every day. I see a lot of folks. We have to always remember for the person in front of us. We're there only. They're not seeing a lot of ALJs and they're not seeing a lot of attorneys. And for them these benefits are life changing. They're dealing with an illness or an injury it's catastrophic. They're begging for help. They're people. Even if the ALJ doesn't believe what they're saying, please always remember this is just another human being in front of you who deserves our time and attention. Will Yang (41:27) And what do do on the day after a case when it doesn't go your way? Diane Haar (41:33) I appeal it. I'm really sore loser. I Will Yang (41:37) you Diane Haar (41:38) don't like to lose. So a lot of the times the appeals, and I'm saying this in case any of the ALJs are listening, I hate to say. Because think I'm right, because I know I'm right. Because my client needs benefits. So the day after I've lost, I'll admit sometimes the losses are a huge shock. Sometimes they're a gut punch. There are times where there have been tears. But the day after, I'm feeling it. Will Yang (42:00) What is something that a client said in a hearing that you'll never forget? Diane Haar (42:04) Actually, this one was after a hearing. There's a lot of things that I've had clients say that I'll never forget. Some tragic and some heartwarming and some really hysterically funny. But This was said to me after a hearing, and it's so true, and it's so true so often. And what he said was, I wrote it down. When I was well, I helped so many people, I never turned them away. Then when I got sick, there was no one there who would help me. And I remember him saying that. He was crying to me when he said it. And I remember it and it was burned into my brain because it hurt hearing him say this. And it was so true of so many people. But you know, One of the things I love about telling you that is this guy showed up at my office a year later, and he brought me, it was around Easter time, so he brought me some chocolate covered Reese's Easter eggs. And it was also to tell me he was super excited. He'd been homeless and he was housed. And he had a friend who was a paraplegic and he was in a wheelchair. And I guess he kept sliding out of it, and he was super excited because he had just fixed up his wheelchair so this guy wasn't gonna slide out of it anymore. He could stay in his chair because he didn't have legs, so he he needed a little extra help there. But he's telling me about his housing and the his friend, and he's he's giving me these chocolate peanut butter Easter eggs. And seeing that smile, like he had a life. You know? And at the end of the day that's why we're really doing this. Like the words that he said are so true. I'm so glad I could be there for him and I wasn't the only one. I'm not the you know, I'm not the savior. I was a cog in the machine that helped helped him get h to where he needed to be. But I'm so grateful for the opportunity. Will Yang (43:35) Yeah, that's a great place for us to wrap up. Really takes us back to even your own personal experience back when you were in your own time of need and like those that were able to help you most as well. Diane, if folks want to get in touch with you, what is the best way that they can reach out and learn more about you? Diane Haar (43:50) Another great way is there's a website, you can reach out to me through the law firm website because I will see it. You're welcome to call. Just reach out any way you want and we can connect. But I hope for anyone looking at this who's thinking about starting a practice, I would reiterate, set your time period and don't quit before then. Will Yang (44:08) Awesome. Thank you so much, Diane. Appreciate the time today. Diane Haar (44:10) Thanks, Will.

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